Ferulic acid is a
hydroxycinnamic acid; it is an organic compound with the formula (CH3O)HOC6H3CH=CHCO2H. The name is derived from the genus Ferula, referring to the giant fennel (Ferula communis). Classified as a
phenolicphytochemical, ferulic acid is an amber colored solid. Esters of ferulic acid are found in plant
cell walls, covalently bonded to
hemicellulose such as
arabinoxylans.[2] Salts and esters derived from ferulic acid are called ferulates.
In cereals, ferulic acid is localized in the
bran – the hard outer layer of grain. In
wheat, phenolic compounds are mainly found in the form of insoluble bound ferulic acid and may be relevant to resistance to wheat fungal diseases.[6] The highest known concentration of ferulic acid
glucoside has been found in
flaxseed (4.1±0.2 g/kg).[7] It is also found in
barley grain.[8]
Asterideudicot plants can also produce ferulic acid. The tea brewed from the leaves of
yacón (Smallanthus sonchifolius), a plant traditionally grown in the northern and central
Andes, contains quantities of ferulic acid. In
legumes, the white bean variety
navy bean is the richest source of ferulic acid among the common bean (Phaseolus vulgaris) varieties.[9] It is also found in
horse grams (Macrotyloma uniflorum).[citation needed]
Although there are many sources of ferulic acid in nature, its
bioavailability depends on the form in which it is present: free ferulic acid has limited solubility in water, and hence poor bioavailability. In wheat grain, ferulic acid is found bound to
cell wallpolysaccharides, allowing it to be released and absorbed in the small intestine.[10]
In a proposed ferulic acid biosynthetic pathway for Escherichia coli, L-tyrosine is converted to
4-coumaric acid by
tyrosine ammonia lyase, which is converted to caffeic acid by Sam5, which is then converted to ferulic acid by caffeic acid methyltransferase.[18]
Ferulic acid, together with
dihydroferulic acid, is a component of
lignocellulose, serving to crosslink the lignin and polysaccharides, thereby conferring rigidity to the cell walls.[19]
It is an intermediate in the synthesis of
monolignols, the monomers of
lignin, and is also used for the synthesis of
lignans.
^Gelinas, Pierre; McKinnon, Carole M. (2006). "Effect of wheat variety, farming site, and bread-baking on total phenolics". International Journal of Food Science and Technology. 41 (3): 329–332.
doi:
10.1111/j.1365-2621.2005.01057.x.
^Beejmohun, Vickram; Fliniaux, Ophélie (2007). "Microwave-assisted extraction of the main phenolic compounds in flaxseed". Phytochemical Analysis. 18 (4): 275–285.
doi:
10.1002/pca.973.
PMID17623361.
^Quinde-Axtell, Zory; Baik, Byung-Kee (2006). "Phenolic Compounds of Barley Grain and Their Implication in Food Product Discoloration". J. Agric. Food Chem. 54 (26): 9978–84.
doi:
10.1021/jf060974w.
PMID17177530.
^Luthria, Devanand L.; Pastor-Corrales, Marcial A. (2006). "Phenolic acids content of fifteen dry edible bean (Phaseolus vulgaris L.) varieties". Journal of Food Composition and Analysis. 19 (2–3): 205–211.
doi:
10.1016/j.jfca.2005.09.003.
^Anson, Nuria Mateo; van den Berg, Robin; Bast, Aalt; Haenen, Guido R. M. M. (2009). "Bioavailability of ferulic acid is determined by its bioaccessibility". Journal of Cereal Science. 49 (2): 296–300.
doi:
10.1016/j.jcs.2008.12.001.
^Valentão, P.; Fernandes, E.; Carvalho, F.; Andrade, P. B.; Seabra, R. M.; Bastos, M. L. (2001). "Antioxidant Activity of Centaurium erythraea Infusion Evidenced by Its Superoxide Radical Scavenging and Xanthine Oxidase Inhibitory Activity". Journal of Agricultural and Food Chemistry. 49 (7): 3476–3479.
doi:
10.1021/jf001145s.
PMID11453794.
^Orthoefer, F. T. (2005).
"Chapter 10: Rice Bran Oil". In Shahidi, F. (ed.). Bailey's Industrial Oil and Fat Products. Vol. 2 (6th ed.). John Wiley & Sons, Inc. p. 465.
ISBN978-0-471-38552-3. Retrieved 2012-03-01.
^Boskov Hansen, H.; Andreasen, M.; Nielsen, M.; Larsen, L.; Knudsen, Bach K.; Meyer, A.; Christensen, L.; Hansen, Å. (2014). "Changes in dietary fibre, phenolic acids and activity of endogenous enzymes during rye bread-making". European Food Research and Technology. 214 (1): 33–42.
doi:
10.1007/s00217-001-0417-6.
ISSN1438-2377.
S2CID85239461.
^Buranov, Anvar U.; Mazza, G. (2009). "Extraction and purification of ferulic acid from flax shives, wheat and corn bran by alkaline hydrolysis and pressurised solvents". Food Chemistry. 115 (4): 1542–1548.
doi:
10.1016/j.foodchem.2009.01.059.